easternshoremdfineproperties.com Search Results

$179,000

1.5 +/- acres perc approved building lot located in Royal Oak Md. Located minutes from St. Michaels and Easton Md and only a short drive to the Oxford / Bellevue Ferry. A perfect opportunity to build your eastern shore dream home in a rural setting while enjoying 5-star dining and amenities only a short drive away. Building lots of this caliber are rare in the county and do not come available often.

Deep Neck Rd, Royal Oak

Listing courtesy of Meredith Fine Properties. Contact: 4108226272

$9,950,000

Set on the coveted shores of the Tred Avon River, this extraordinary waterfront estate is a rare offering, combining deep-water boating, a private sandy beach, a substantial main residence, separate guest accommodations, and an exceptional collection of lifestyle amenities. From the first approach, the property unfolds as a private Eastern Shore compound, where elegant architecture, sweeping river views, and resort-caliber amenities are seamlessly integrated into a singular waterfront setting. The four-bedroom, five-and-a-half-bath main residence is both impressive and inviting. A dramatic two-story living room features hardwood floors, a fireplace, custom millwork, and abundant natural light, while the waterside den offers a more intimate retreat with a gas fireplace, custom bookshelves, and a wall of glass framing views across the Tred Avon. A spacious screened porch and expansive Ipe decking extend the living spaces outdoors and provide direct access to the waterfront. At the heart of the home, the kitchen is equipped with a Sub-Zero refrigerator, gas cooktop, double ovens, stainless steel dishwasher, granite countertops, and white cabinetry, along with generous space for casual dining. A first-floor office and laundry room add everyday convenience, while dual staircases provide easy access throughout the home. The first-floor waterfront primary suite is a private sanctuary with its own fireplace, sitting room with custom bookshelves, two walk-in closets with custom shelving, and a beautifully appointed bath featuring a waterside soaking tub, dual vanity, and walk-in steam shower. Each additional bedroom is en suite, creating comfortable and private accommodations for family and guests. Outside, the property transforms into a private waterfront retreat. A heated lap pool, hot tub, and sandy beach create distinct places to relax along the river, while a scenic walking path winds through wildflower gardens and open space, reinforcing the estate’s remarkable sense of privacy and scale. The pool house makes outdoor entertaining effortless, with a full kitchen, stainless steel appliances, gas range, laundry facilities, and an outdoor shower. A separate three-bedroom, two-bath guest residence provides exceptional additional accommodations with hardwood floors, a full kitchen, laundry, garage, and a large deck overlooking the Tred Avon—ideal for extended family, guests, or multi-generational living while preserving the privacy of the main residence. For those drawn to the water, the property delivers. A private pier offers 6+ feet of water at mean low water, three slips, two boat lifts, water and electric—providing exceptional deep-water access for a wide range of vessels. From here, spend the day cruising the Tred Avon and exploring the waterways of the Chesapeake Bay. A rip-rapped shoreline provides protection while preserving the property’s connection to the river. With a three-car garage, irrigation system, extensive custom millwork, guest and pool houses, heated pool, sandy beach, and substantial boating infrastructure, this is far more than a waterfront home. It is a complete Eastern Shore estate—a private compound where the residences, grounds, and waterfront amenities come together to create an exceptional lifestyle on the Tred Avon.

4 Beds ⋅ 6 Baths

Set on the coveted shores of the Tred Avon River, this extraordinary waterfront estate is a rare offering, combining deep-water boating, a private sandy beach, a substantial main residence, separate guest accommodations, and an exceptional collection of lifestyle amenities. From the first approach, the property unfolds as a private Eastern Shore compound, where elegant architecture, sweeping river views, and resort-caliber amenities are seamlessly integrated into a singular waterfront setting. The four-bedroom, five-and-a-half-bath main residence is both impressive and inviting. A dramatic two-story living room features hardwood floors, a fireplace, custom millwork, and abundant natural light, while the waterside den offers a more intimate retreat with a gas fireplace, custom bookshelves, and a wall of glass framing views across the Tred Avon. A spacious screened porch and expansive Ipe decking extend the living spaces outdoors and provide direct access to the waterfront. At the heart of the home, the kitchen is equipped with a Sub-Zero refrigerator, gas cooktop, double ovens, stainless steel dishwasher, granite countertops, and white cabinetry, along with generous space for casual dining. A first-floor office and laundry room add everyday convenience, while dual staircases provide easy access throughout the home. The first-floor waterfront primary suite is a private sanctuary with its own fireplace, sitting room with custom bookshelves, two walk-in closets with custom shelving, and a beautifully appointed bath featuring a waterside soaking tub, dual vanity, and walk-in steam shower. Each additional bedroom is en suite, creating comfortable and private accommodations for family and guests. Outside, the property transforms into a private waterfront retreat. A heated lap pool, hot tub, and sandy beach create distinct places to relax along the river, while a scenic walking path winds through wildflower gardens and open space, reinforcing the estate’s remarkable sense of privacy and scale. The pool house makes outdoor entertaining effortless, with a full kitchen, stainless steel appliances, gas range, laundry facilities, and an outdoor shower. A separate three-bedroom, two-bath guest residence provides exceptional additional accommodations with hardwood floors, a full kitchen, laundry, garage, and a large deck overlooking the Tred Avon—ideal for extended family, guests, or multi-generational living while preserving the privacy of the main residence. For those drawn to the water, the property delivers. A private pier offers 6+ feet of water at mean low water, three slips, two boat lifts, water and electric—providing exceptional deep-water access for a wide range of vessels. From here, spend the day cruising the Tred Avon and exploring the waterways of the Chesapeake Bay. A rip-rapped shoreline provides protection while preserving the property’s connection to the river. With a three-car garage, irrigation system, extensive custom millwork, guest and pool houses, heated pool, sandy beach, and substantial boating infrastructure, this is far more than a waterfront home. It is a complete Eastern Shore estate—a private compound where the residences, grounds, and waterfront amenities come together to create an exceptional lifestyle on the Tred Avon.

6920 Travelers Rest Cir, Easton

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600

$1,075,000

This spacious 4-bedroom, 3.5-bath home offers a peaceful rural setting just minutes from downtown Easton. Set on 2+/- acres with an additional 5.92+/-acre non-buildable lot included in the sale, the property offers plenty of space both inside and out. The main level features a large living room with a stone-surround gas fireplace, formal dining room, sunroom, and a well-appointed kitchen with stainless steel appliances, and a large island that makes gathering and entertaining easy. A first-floor office or library adds flexibility, while A whole-home Sonos sound system adds another layer of convenience for everyday living and entertaining. Upstairs, the spacious primary suite includes a private bath with a tile-surround shower and soaking tub, along with three additional bedrooms, two of which have attached baths. The full basement is a standout feature, offering a dedicated workshop with ample space for projects, tools, and storage. Outside, the entertaining space continues with a large back porch, pool, hot tub, oversized shed, extended driveway, and lush landscaping. With a secluded country feel, generous indoor and outdoor gathering spaces, and easy access to downtown Easton, this property offers an exceptional balance of privacy, space, and convenience.

4 Beds ⋅ 4 Baths

This spacious 4-bedroom, 3.5-bath home offers a peaceful rural setting just minutes from downtown Easton. Set on 2+/- acres with an additional 5.92+/-acre non-buildable lot included in the sale, the property offers plenty of space both inside and out. The main level features a large living room with a stone-surround gas fireplace, formal dining room, sunroom, and a well-appointed kitchen with stainless steel appliances, and a large island that makes gathering and entertaining easy. A first-floor office or library adds flexibility, while A whole-home Sonos sound system adds another layer of convenience for everyday living and entertaining. Upstairs, the spacious primary suite includes a private bath with a tile-surround shower and soaking tub, along with three additional bedrooms, two of which have attached baths. The full basement is a standout feature, offering a dedicated workshop with ample space for projects, tools, and storage. Outside, the entertaining space continues with a large back porch, pool, hot tub, oversized shed, extended driveway, and lush landscaping. With a secluded country feel, generous indoor and outdoor gathering spaces, and easy access to downtown Easton, this property offers an exceptional balance of privacy, space, and convenience.

29747 Easton Farms, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665

$865,000

A distinctive Eastern Shore residence where historic character, generous living spaces and mature gardens come together in a setting that feels established and remarkably private. The home has evolved, creating a spacious interior with original architectural elements complemented by later additions designed to bring more light and garden views into the house, along with modern conveniences. Wood floors, substantial trim, original wood doors, exposed brick, built-in cabinetry, and bookcases preserve much of the home's character. The main level offers a series of interconnected gathering spaces rather than a conventional modern floor plan. A formal dining room provides a more traditional setting for entertaining, while the large kitchen offers a substantial center island, an informal dining area, and casual living space. The house opens dramatically toward the gardens. The family room is centered around a large brick fireplace and surrounded by built-in bookcases, while broad windows overlook the grounds. An adjoining garden room sits several steps below the principal living level and is wrapped in windows and glazed doors, creating an exceptional transition between indoors and out. Brick flooring reinforces the connection to the adjoining brick terraces and garden. Upstairs, the bedrooms are notably generous in scale, with abundant natural light and the irregularities and details that distinguish an older home from newer construction. Multiple baths serve the upper level, and wood flooring, traditional doors, and architectural details continue throughout. Outside, brick terraces extend the living areas into a mature landscape of lawn, established trees, perennial garden beds, and an ornamental pond. The grounds have the feeling of a garden developed over many years rather than newly installed landscaping. A detached two-car garage provides additional utility and storage with a conditioned second-floor fitness room or studio. Located minutes from downtown Easton and within the rural setting of Talbot County, this new offering is sure to please the discerning buyer.

5 Beds ⋅ 3 Baths

A distinctive Eastern Shore residence where historic character, generous living spaces and mature gardens come together in a setting that feels established and remarkably private. The home has evolved, creating a spacious interior with original architectural elements complemented by later additions designed to bring more light and garden views into the house, along with modern conveniences. Wood floors, substantial trim, original wood doors, exposed brick, built-in cabinetry, and bookcases preserve much of the home's character. The main level offers a series of interconnected gathering spaces rather than a conventional modern floor plan. A formal dining room provides a more traditional setting for entertaining, while the large kitchen offers a substantial center island, an informal dining area, and casual living space. The house opens dramatically toward the gardens. The family room is centered around a large brick fireplace and surrounded by built-in bookcases, while broad windows overlook the grounds. An adjoining garden room sits several steps below the principal living level and is wrapped in windows and glazed doors, creating an exceptional transition between indoors and out. Brick flooring reinforces the connection to the adjoining brick terraces and garden. Upstairs, the bedrooms are notably generous in scale, with abundant natural light and the irregularities and details that distinguish an older home from newer construction. Multiple baths serve the upper level, and wood flooring, traditional doors, and architectural details continue throughout. Outside, brick terraces extend the living areas into a mature landscape of lawn, established trees, perennial garden beds, and an ornamental pond. The grounds have the feeling of a garden developed over many years rather than newly installed landscaping. A detached two-car garage provides additional utility and storage with a conditioned second-floor fitness room or studio. Located minutes from downtown Easton and within the rural setting of Talbot County, this new offering is sure to please the discerning buyer.

30595 Kingston Rd, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 770-9255

$1,500,000

OPEN HOUSE ON SUNDAY FROM 2:00-4:00PM. A stunning Farmhouse completely restored/rebuilt by renown Architect Greg Wiedemann on two glorious acres meticulously maintained on a serene Choptank River Setting. it is the Quintessential "Getaway" from the hustle/bustle of life. The focus of each room is the River. There are patios, balconies and porches galore for your leisure enjoyment and viewing pleasure. The center of the home is the Dining and Kitchen area. You enter from the side porch and exit through either twin glass doors which border large windows which overlook the River onto a flagstone patio where you can enjoy outdoor dining or just relaxing by the River. Off of the Kitchen you will find the "Mud Room" and/or Laundry Room. You will find a stackable Washer Dryer and Utility Sink in this area. Also next to the Laundry room you will find a large full bath with shower. The actual Front Door to the home is on the side of the house off of the welcoming porch with a swing. The Main entrance opens to the Living Room with Large windows which front to the Choptank. One of the four bedrooms in the home is on the first floor with a large ensuite bath, There are actually two large primary bedrooms. One can use the primary bedroom on the first floor for a large family room as the upstairs bedrooms are very spacious. The second floor primary enjoys both a balcony and a screened porch. The home is in excellent condition. The two zone air conditioning systems have just been replaced. On the grounds you will find two sheds, one for utilities and the other serves as a Workshop and storage, Enjoy a 1000 foot private beach front with a dock. Within the photos, please take the time to gaze upon the variety of seasonal trees and flowering plants that adorn this two acre paradise.

4 Beds ⋅ 3 Baths

OPEN HOUSE ON SUNDAY FROM 2:00-4:00PM. A stunning Farmhouse completely restored/rebuilt by renown Architect Greg Wiedemann on two glorious acres meticulously maintained on a serene Choptank River Setting. it is the Quintessential "Getaway" from the hustle/bustle of life. The focus of each room is the River. There are patios, balconies and porches galore for your leisure enjoyment and viewing pleasure. The center of the home is the Dining and Kitchen area. You enter from the side porch and exit through either twin glass doors which border large windows which overlook the River onto a flagstone patio where you can enjoy outdoor dining or just relaxing by the River. Off of the Kitchen you will find the "Mud Room" and/or Laundry Room. You will find a stackable Washer Dryer and Utility Sink in this area. Also next to the Laundry room you will find a large full bath with shower. The actual Front Door to the home is on the side of the house off of the welcoming porch with a swing. The Main entrance opens to the Living Room with Large windows which front to the Choptank. One of the four bedrooms in the home is on the first floor with a large ensuite bath, There are actually two large primary bedrooms. One can use the primary bedroom on the first floor for a large family room as the upstairs bedrooms are very spacious. The second floor primary enjoys both a balcony and a screened porch. The home is in excellent condition. The two zone air conditioning systems have just been replaced. On the grounds you will find two sheds, one for utilities and the other serves as a Workshop and storage, Enjoy a 1000 foot private beach front with a dock. Within the photos, please take the time to gaze upon the variety of seasonal trees and flowering plants that adorn this two acre paradise.

31720 Ayres Dr, Trappe

Listing courtesy of Weichert, REALTORS. Contact: afitzgerald@weichertrealtors.net

$6,375,000

Duvall Farm is a rare Eastern Shore offering — a 408± acre farm that blends meaningful conservation efforts with immense easement potential, productive farmland, and refined residential improvements in a location between Easton and Oxford. Significant in both scale and character, the farm is comprised of 20 recorded parcels, presenting long-term value and a wide range of opportunities. The land itself is remarkable. With significant acreage enrolled in the Conservation Reserve Program, over 185± acres provide restored habitat for wildlife and waterfowl. Another 50± acres remain under active cultivation, sustaining the farm’s agricultural heritage. The balance of the property presents a diverse mix of wetlands, mature woodland, wooded buffers, upland habitat, and scenic fields. These varied landscapes support habitat restoration and sporting use, while offering beautiful vistas in every season. A carefully maintained network of trails, and farm lanes provide access throughout the property, making it well-suited for recreation, hunting, and conservation management. At the heart of Duvall Farm is Duvall Lodge, constructed in 2006 by Ilex Construction. Drawing inspiration from Tennessee Pioneer architecture, the lodge is both timeless and inviting. The design embraces rustic authenticity while incorporating every modern comfort. Inside, the great room makes a dramatic impression with soaring ceilings, reclaimed timbers, wide-plank wood floors, and a massive stone fireplace that anchors the space. Exposed beams and natural materials create a warm ambiance, while broad windows and doors seamlessly connect the interior to the surrounding landscape. One of the lodge’s defining features is its full wraparound screened porch, offering sweeping views over a tranquil pond, stocked with bass and with a small pier. Whether for quiet mornings or gatherings with friends, the porch underscores the property’s seamless blend of indoor and outdoor living. Nearby, a hand-hewn log guest cabin extends the accommodations, creating a setting well suited to hosting family and friends. The improvements are understated yet thoughtful, designed to complement rather than dominate the landscape. They reflect the same stewardship evident across the farm itself — an approach that values authenticity, conservation, and the enduring character of the land. Duvall Farm is more than acreage; it is a complete environment, where agricultural productivity, habitat diversity, and architectural charm intersect. Few properties on Maryland’s Eastern Shore offer this combination of size, recorded parcels, conservation value, and a central lodge that feels historic with modern amenities. The location, just minutes from Easton and Oxford, places Duvall Farm within easy reach of the region’s cultural and culinary attractions, while the sheer scale of the farm ensures privacy and a retreat-like atmosphere. For those seeking a legacy property, conservation showcase, sporting retreat, or family compound, Duvall Farm represents an unparalleled opportunity. With its rich mix of land, water, and architecture, it is a property of enduring importance — one that honors the past while offering a wide horizon for the future. Please Note, tax ID and Property Taxes are showing the information on record for the improved parcel. Please contact agent for additional parcel information.

2 Beds ⋅ 3 Baths

Duvall Farm is a rare Eastern Shore offering — a 408± acre farm that blends meaningful conservation efforts with immense easement potential, productive farmland, and refined residential improvements in a location between Easton and Oxford. Significant in both scale and character, the farm is comprised of 20 recorded parcels, presenting long-term value and a wide range of opportunities. The land itself is remarkable. With significant acreage enrolled in the Conservation Reserve Program, over 185± acres provide restored habitat for wildlife and waterfowl. Another 50± acres remain under active cultivation, sustaining the farm’s agricultural heritage. The balance of the property presents a diverse mix of wetlands, mature woodland, wooded buffers, upland habitat, and scenic fields. These varied landscapes support habitat restoration and sporting use, while offering beautiful vistas in every season. A carefully maintained network of trails, and farm lanes provide access throughout the property, making it well-suited for recreation, hunting, and conservation management. At the heart of Duvall Farm is Duvall Lodge, constructed in 2006 by Ilex Construction. Drawing inspiration from Tennessee Pioneer architecture, the lodge is both timeless and inviting. The design embraces rustic authenticity while incorporating every modern comfort. Inside, the great room makes a dramatic impression with soaring ceilings, reclaimed timbers, wide-plank wood floors, and a massive stone fireplace that anchors the space. Exposed beams and natural materials create a warm ambiance, while broad windows and doors seamlessly connect the interior to the surrounding landscape. One of the lodge’s defining features is its full wraparound screened porch, offering sweeping views over a tranquil pond, stocked with bass and with a small pier. Whether for quiet mornings or gatherings with friends, the porch underscores the property’s seamless blend of indoor and outdoor living. Nearby, a hand-hewn log guest cabin extends the accommodations, creating a setting well suited to hosting family and friends. The improvements are understated yet thoughtful, designed to complement rather than dominate the landscape. They reflect the same stewardship evident across the farm itself — an approach that values authenticity, conservation, and the enduring character of the land. Duvall Farm is more than acreage; it is a complete environment, where agricultural productivity, habitat diversity, and architectural charm intersect. Few properties on Maryland’s Eastern Shore offer this combination of size, recorded parcels, conservation value, and a central lodge that feels historic with modern amenities. The location, just minutes from Easton and Oxford, places Duvall Farm within easy reach of the region’s cultural and culinary attractions, while the sheer scale of the farm ensures privacy and a retreat-like atmosphere. For those seeking a legacy property, conservation showcase, sporting retreat, or family compound, Duvall Farm represents an unparalleled opportunity. With its rich mix of land, water, and architecture, it is a property of enduring importance — one that honors the past while offering a wide horizon for the future. Please Note, tax ID and Property Taxes are showing the information on record for the improved parcel. Please contact agent for additional parcel information.

6150 Oxford Rd, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 770-9255

$1,000,000

Built in 2006 and meticulously maintained, this exceptional home offers 6,553 square feet of living space, including 4,463 square feet above grade and an additional 2,090 square feet in the finished walk-out basement with both interior and exterior access. Inside, a dramatic two-story foyer and soaring family room create an impressive sense of openness, while oversized windows fill the home with abundant natural light. The thoughtfully designed floor plan includes formal living and dining rooms, as well as inviting spaces for everyday living and entertainment. A private first-floor office offers flexibility to serve as a main-level bedroom if desired. Dual staircases provide convenient access to the second level. The gourmet kitchen features beautiful 42-inch cabinetry, Corian countertops, a center island, and a sunny breakfast room with a door leading to the backyard, making indoor-outdoor entertainment effortless. The spacious primary suite is a true retreat, highlighted by a coffered ceiling, a generous walk-in closet, and a luxurious en-suite bath. The second floor offers four bedrooms and three baths. The finished basement expands the living space with a full bathroom and endless possibilities for recreation, entertaining, or multi-generational living. Situated on a private lot backing to open space, the property extends beyond the wrought iron fenced around the gunite pool, into a serene stand of mature pine trees, creating a peaceful and picturesque setting. The professionally landscaped grounds feature lush flower beds with an irrigation system, extensive hardscaping surrounding the gunite pool, patio, and a wraparound porch on the front, catches all the curb appeal you want, paved driveway leading to the side-entry garage. Additional highlights include an epoxy-coated garage floor with an organized wall storage system, professional-grade landscaping, and exceptional pride of ownership throughout. This home shows like a new offering the quality and feel of new construction without the wait. Despite its remarkably quiet and private setting, the home is conveniently located just minutes from shopping, dining, community events, water access, major commuter routes, offering the perfect balance of tranquility and accessibility. So, if you are ready to design your new life style or have a second home, come see this beautiful home.

4 Beds ⋅ 5 Baths

Built in 2006 and meticulously maintained, this exceptional home offers 6,553 square feet of living space, including 4,463 square feet above grade and an additional 2,090 square feet in the finished walk-out basement with both interior and exterior access. Inside, a dramatic two-story foyer and soaring family room create an impressive sense of openness, while oversized windows fill the home with abundant natural light. The thoughtfully designed floor plan includes formal living and dining rooms, as well as inviting spaces for everyday living and entertainment. A private first-floor office offers flexibility to serve as a main-level bedroom if desired. Dual staircases provide convenient access to the second level. The gourmet kitchen features beautiful 42-inch cabinetry, Corian countertops, a center island, and a sunny breakfast room with a door leading to the backyard, making indoor-outdoor entertainment effortless. The spacious primary suite is a true retreat, highlighted by a coffered ceiling, a generous walk-in closet, and a luxurious en-suite bath. The second floor offers four bedrooms and three baths. The finished basement expands the living space with a full bathroom and endless possibilities for recreation, entertaining, or multi-generational living. Situated on a private lot backing to open space, the property extends beyond the wrought iron fenced around the gunite pool, into a serene stand of mature pine trees, creating a peaceful and picturesque setting. The professionally landscaped grounds feature lush flower beds with an irrigation system, extensive hardscaping surrounding the gunite pool, patio, and a wraparound porch on the front, catches all the curb appeal you want, paved driveway leading to the side-entry garage. Additional highlights include an epoxy-coated garage floor with an organized wall storage system, professional-grade landscaping, and exceptional pride of ownership throughout. This home shows like a new offering the quality and feel of new construction without the wait. Despite its remarkably quiet and private setting, the home is conveniently located just minutes from shopping, dining, community events, water access, major commuter routes, offering the perfect balance of tranquility and accessibility. So, if you are ready to design your new life style or have a second home, come see this beautiful home.

13446 Blackberry Ln, Wye Mills

Listing courtesy of Coldwell Banker Realty. Contact: kelly.thompson@cbmove.com

$410,000

Experience authentic Eastern Shore living in this peaceful Chesapeake Bay retreat, located just steps from historic Dogwood Harbour, home to the Skipjacks—the last working commercial sailing fleet in the United States. This charming home features three first-floor bedrooms and a full bath, providing comfortable one-level living for family and guests. The remodeled eat-in kitchen showcases granite countertops and opens to a spacious outdoor deck, perfect for entertaining or relaxing while enjoying the coastal atmosphere. Upstairs, the private primary suite offers a full bath with a spa tub, creating a tranquil retreat. Also on the second level is an expansive open living area complete with a half bath and wet bar, providing exceptional flexibility for entertaining, recreation, a home office, or additional guest accommodations. Recent improvements include a new roof (2026), luxury vinyl plank flooring throughout, a new washer and dryer, a new stove/range, and a new central heating and air conditioning system, offering peace of mind and modern comfort. Combining historic waterfront charm with thoughtful updates, this property presents a rare opportunity to enjoy the best of Chesapeake Bay living, whether as a full-time residence, weekend getaway, or investment property. The owner is a licensed Maryland Real Estate agent.

4 Beds ⋅ 3 Baths

Experience authentic Eastern Shore living in this peaceful Chesapeake Bay retreat, located just steps from historic Dogwood Harbour, home to the Skipjacks—the last working commercial sailing fleet in the United States. This charming home features three first-floor bedrooms and a full bath, providing comfortable one-level living for family and guests. The remodeled eat-in kitchen showcases granite countertops and opens to a spacious outdoor deck, perfect for entertaining or relaxing while enjoying the coastal atmosphere. Upstairs, the private primary suite offers a full bath with a spa tub, creating a tranquil retreat. Also on the second level is an expansive open living area complete with a half bath and wet bar, providing exceptional flexibility for entertaining, recreation, a home office, or additional guest accommodations. Recent improvements include a new roof (2026), luxury vinyl plank flooring throughout, a new washer and dryer, a new stove/range, and a new central heating and air conditioning system, offering peace of mind and modern comfort. Combining historic waterfront charm with thoughtful updates, this property presents a rare opportunity to enjoy the best of Chesapeake Bay living, whether as a full-time residence, weekend getaway, or investment property. The owner is a licensed Maryland Real Estate agent.

21406 Dogwood Cove Rd, Tilghman

Listing courtesy of Meredith Fine Properties. Contact: 4107149166

$3,995,000

Experience refined waterfront living in this stunning Lowcountry-style estate, gracefully set on an exceptional waterfront lot among mature Loblolly pines with a coveted southern exposure. Offering sweeping, unobstructed water views, and a rare sense of privacy, the property is bathed in natural light throughout the day, with breathtaking sunrises and and warm, golden reflections in the evening. This 3,800 square foot main residence is complimented by a beautifully appointed 1,200 sq. foot guest cottage, creating an ideal balance of elegance and hospitality. The guest cottage serves as a private retreat, complete with a comfortable living room, galley kitchen, three bedrooms, and a screened porch for quiet relaxation. Inside, timeless craftsmanship defines every space, from reclaimed oak flooring to granite countertops and a meticulously maintained cedar exterior. Outdoors, the lifestyle continues with resort style amenities, including a sparkling in-ground pool, hot tub, firepit and a private 120 foot pier with approximately 7 feet of depth at mean low water- offering effortless access for boating fishing, and enjoying the very best of waterfront living. A rare offering where exceptional land, elegant design, and an unparalleled coastal lifestyle come together.

5 Beds ⋅ 4 Baths

Experience refined waterfront living in this stunning Lowcountry-style estate, gracefully set on an exceptional waterfront lot among mature Loblolly pines with a coveted southern exposure. Offering sweeping, unobstructed water views, and a rare sense of privacy, the property is bathed in natural light throughout the day, with breathtaking sunrises and and warm, golden reflections in the evening. This 3,800 square foot main residence is complimented by a beautifully appointed 1,200 sq. foot guest cottage, creating an ideal balance of elegance and hospitality. The guest cottage serves as a private retreat, complete with a comfortable living room, galley kitchen, three bedrooms, and a screened porch for quiet relaxation. Inside, timeless craftsmanship defines every space, from reclaimed oak flooring to granite countertops and a meticulously maintained cedar exterior. Outdoors, the lifestyle continues with resort style amenities, including a sparkling in-ground pool, hot tub, firepit and a private 120 foot pier with approximately 7 feet of depth at mean low water- offering effortless access for boating fishing, and enjoying the very best of waterfront living. A rare offering where exceptional land, elegant design, and an unparalleled coastal lifestyle come together.

4335 World Farm Rd, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415

$60,000

Build your dream home on beautiful Tilghman Island! This ideally located lot is within walking distance of Sinclair Community Park, local marinas, charming shops, and popular waterfront restaurants. Stroll to the end of your street to enjoy stunning Chesapeake Bay sunsets from the park’s scenic shoreline. Tilghman Island is a beloved Eastern Shore destination known for its rich maritime heritage, working harbor, and friendly small-town atmosphere. Residents and visitors alike enjoy boating, fishing, kayaking, crabbing, and biking along quiet country roads. The island offers a relaxed coastal lifestyle while still being only a short drive to St. Michaels and other Bay communities. Public sewer connection available, making the building process straightforward and convenient. Don’t miss this opportunity to own a piece of island life—perfect for a full-time residence or a serene getaway by the Bay.

Sinclair Ave, Tilghman

Listing courtesy of Meredith Fine Properties. Contact: 4107149166

$5,995,000

Wilderness Estate- This quintessential Eastern Shore farm is located along the Choptank River in Trappe, Maryland. Comprised of 47± acres, with original structures that are impeccably well-kept and improved with modern amenities, The Wilderness provides a unique opportunity to enjoy the best of the Eastern Shore. Surrounded by open space and preserved farmland with proximity to Oxford, Easton, Cambridge, and St. Michaels, The Wilderness is sure to please the discerning buyer. Sited among large waterfront estates, The Wilderness enjoys privacy and a commanding presence with old-growth trees, broad southerly views, and deep water. The scope of improvements includes the primary residence, waterside guest cottage, beach house, pool, pier, tennis court, early 20th-century barn, and a host of accessory structures for life on the farm. Visit the virtual tour for an inside look. The main house has great historical significance not only for the original owner’s grandson who lived there and served two terms as the Governor of Maryland but also for its place in the development of Maryland’s domestic architecture, as noted on two markers from the Maryland Bicentennial Commission and the Maryland Historical Society. The smaller and original of the two brick wings dates from the late 18th century and the larger wing from the early 19th century. The house’s architecture is unusual in that the 19th-century wings telescope up, instead of down, from the original wing. The white brick, black shutters, and historical olive green trim color are a serene palette against the house’s majestic specimen trees around the property, including a gigantic Sycamore that was at one time, the largest of its species in Maryland. The long white gravel drive under the sheltering canopy of mature trees passes by the barn and other outbuildings then curves around the front of the house. Brick steps lead up to the front porch of the early 19th century wing opening into a gracious foyer and stair hall with an elegant elliptical arch that rests on pilasters at the side walls to separate the public from private areas of the house. A French door at the rear of the foyer frames a vista of the lawn and Choptank River. To the side of the foyer are two identical parlors at the front and rear corners of the house. Both rooms have magnificent fireplace mantles and surround; one is a 1740 hand-carved mantel by noted English artisan woodcarver Grinnling Gibbons and the other is a 1780 mantel surrounded by the famous English architect and artisan, Robert Adam. The main floor of the 18th-century wing contains a spacious living room, dining room, original kitchen, and larger kitchen, pantry, two powder rooms, and a stunning sunroom connecting to a terrace along the rear of the house overlooking the Choptank River. Part of this wing was the final addition to the original home. The second floor of the 19th-century wing contains two bedrooms over the two parlors below with fireplaces and walk-in closets and two baths. The 18th-century wing and later addition contain an artist’s studio with cabinetry and sink that has a myriad uses– TV room, arts and crafts room. The primary suite is located at the rear corner of this wing. It has a fireplace flanked by single windows and another window on the rear wall for panoramic views of the mature landscape and the Choptank River. Two baths complete the suite, with one bath off a hall for access from the art studio. Two stairs access the attic level; one in the 18th-century wing leads to two bedrooms and one bath. The main stair in the 19th-century wing leads to a large game room and another cozy bedroom ensuite.

6 Beds ⋅ 6 Baths

Wilderness Estate- This quintessential Eastern Shore farm is located along the Choptank River in Trappe, Maryland. Comprised of 47± acres, with original structures that are impeccably well-kept and improved with modern amenities, The Wilderness provides a unique opportunity to enjoy the best of the Eastern Shore. Surrounded by open space and preserved farmland with proximity to Oxford, Easton, Cambridge, and St. Michaels, The Wilderness is sure to please the discerning buyer. Sited among large waterfront estates, The Wilderness enjoys privacy and a commanding presence with old-growth trees, broad southerly views, and deep water. The scope of improvements includes the primary residence, waterside guest cottage, beach house, pool, pier, tennis court, early 20th-century barn, and a host of accessory structures for life on the farm. Visit the virtual tour for an inside look. The main house has great historical significance not only for the original owner’s grandson who lived there and served two terms as the Governor of Maryland but also for its place in the development of Maryland’s domestic architecture, as noted on two markers from the Maryland Bicentennial Commission and the Maryland Historical Society. The smaller and original of the two brick wings dates from the late 18th century and the larger wing from the early 19th century. The house’s architecture is unusual in that the 19th-century wings telescope up, instead of down, from the original wing. The white brick, black shutters, and historical olive green trim color are a serene palette against the house’s majestic specimen trees around the property, including a gigantic Sycamore that was at one time, the largest of its species in Maryland. The long white gravel drive under the sheltering canopy of mature trees passes by the barn and other outbuildings then curves around the front of the house. Brick steps lead up to the front porch of the early 19th century wing opening into a gracious foyer and stair hall with an elegant elliptical arch that rests on pilasters at the side walls to separate the public from private areas of the house. A French door at the rear of the foyer frames a vista of the lawn and Choptank River. To the side of the foyer are two identical parlors at the front and rear corners of the house. Both rooms have magnificent fireplace mantles and surround; one is a 1740 hand-carved mantel by noted English artisan woodcarver Grinnling Gibbons and the other is a 1780 mantel surrounded by the famous English architect and artisan, Robert Adam. The main floor of the 18th-century wing contains a spacious living room, dining room, original kitchen, and larger kitchen, pantry, two powder rooms, and a stunning sunroom connecting to a terrace along the rear of the house overlooking the Choptank River. Part of this wing was the final addition to the original home. The second floor of the 19th-century wing contains two bedrooms over the two parlors below with fireplaces and walk-in closets and two baths. The 18th-century wing and later addition contain an artist’s studio with cabinetry and sink that has a myriad uses– TV room, arts and crafts room. The primary suite is located at the rear corner of this wing. It has a fireplace flanked by single windows and another window on the rear wall for panoramic views of the mature landscape and the Choptank River. Two baths complete the suite, with one bath off a hall for access from the art studio. Two stairs access the attic level; one in the 18th-century wing leads to two bedrooms and one bath. The main stair in the 19th-century wing leads to a large game room and another cozy bedroom ensuite.

27293 Southside Island Creek Rd, Trappe

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 770-9255

$470,000

Unique, one-of-a-kind property located in the heart of Tilghman Island, offering unparalleled tranquility and breathtaking water views overlooking Dogwood Harbor. Welcome to your private Eastern Shore retreat! This beautifully updated water-view home captures the essence of coastal living with sweeping views of the harbor and surrounding wildlife. Enjoy stunning sunsets and peaceful mornings from the expansive screened porch or spacious deck—perfect for relaxing or entertaining while taking in the natural beauty of the island. Inside, the home has been thoughtfully updated and features a bright, open living area and a beautifully renovated kitchen designed for both everyday living and gatherings with family and friends. The spacious primary suite offers a private bath and walk-in closet, along with panoramic water views and direct access to the second-story porch/deck with a retractable awning—an ideal place to unwind and enjoy the serene surroundings. Two additional guest bedrooms and a full bath complete the home’s comfortable and functional layout. Additional highlights include a charming screened porch, generous outdoor living spaces, a storage shed, and beautifully landscaped patios and walkways that enhance the home’s inviting coastal atmosphere. Located in the heart of Tilghman Island, this exceptional property offers the perfect opportunity to relax, boat, fish, and explore everything the Eastern Shore lifestyle has to offer.

3 Beds ⋅ 3 Baths

Unique, one-of-a-kind property located in the heart of Tilghman Island, offering unparalleled tranquility and breathtaking water views overlooking Dogwood Harbor. Welcome to your private Eastern Shore retreat! This beautifully updated water-view home captures the essence of coastal living with sweeping views of the harbor and surrounding wildlife. Enjoy stunning sunsets and peaceful mornings from the expansive screened porch or spacious deck—perfect for relaxing or entertaining while taking in the natural beauty of the island. Inside, the home has been thoughtfully updated and features a bright, open living area and a beautifully renovated kitchen designed for both everyday living and gatherings with family and friends. The spacious primary suite offers a private bath and walk-in closet, along with panoramic water views and direct access to the second-story porch/deck with a retractable awning—an ideal place to unwind and enjoy the serene surroundings. Two additional guest bedrooms and a full bath complete the home’s comfortable and functional layout. Additional highlights include a charming screened porch, generous outdoor living spaces, a storage shed, and beautifully landscaped patios and walkways that enhance the home’s inviting coastal atmosphere. Located in the heart of Tilghman Island, this exceptional property offers the perfect opportunity to relax, boat, fish, and explore everything the Eastern Shore lifestyle has to offer.

5933 Tilghman Island Rd, Tilghman

Listing courtesy of Meredith Fine Properties. Contact: 4107149166

$2,500,000

Discover one of Talbot County’s rare farms that combines productive farmland, waterfront, and exceptional recreational opportunities. This 105.72-acre agricultural property features approximately 80± acres of tillable ground and is well suited for continued farming, income production, or long-term land investment. The open farmland is framed by wooded perimeter lines with a mixture of mature hardwoods and softwoods, including pine and oak, providing privacy, scenic beauty, and excellent wildlife habitat. The property is zoned agricultural, offering flexibility for farming, recreation, or investment use. The tillable acreage carries an overall NCCPI rating of approximately 57.3, indicating solid, productive ground suitable for row crops, small grains, and conservation programs. The farm boasts over 2,500 feet of water frontage on Miles Creek, offering excellent duck and goose hunting opportunities. The property is located on a known migratory flyway for ducks and geese along the Chesapeake Bay, making it a proven waterfowl destination. A network of trails through the wooded areas leads to a cleared waterfront area on Miles Creek featuring a dock and picnic table, ideal for family activities, swimming, and fishing. A small point along the creek includes a strategically placed booby blind, positioned for effective duck and goose hunting. Additional amenities include multiple duck blinds on Miles Creek and a goose pit. The historic two-story farmhouse, dating to the early 1900s, offers five bedrooms and one full bathroom and features a new roof and siding. Beginning with the main floor, the home offers a large living room, dining room, kitchen, and the first of five bedrooms. The second floor includes four large bedrooms and a full bath. The residence is accessed by a private driveway off Saulsbury Road, providing convenient access while maintaining a high level of privacy. A small shed next to the home provides additional storage. This property is income-producing, with revenue potential from farming operations, CRP enrollment, and hunting leases, making it a versatile investment opportunity, productive farm, or private recreational retreat with waterfront access. Property is being offered in cooperation with Casey Kennedy and Whitetail Properties.

4108 Saulsbury Rd, Trappe

Listing courtesy of VYBE Realty. Contact: 4102204648

$2,500,000

Discover one of Talbot County’s rare farms that combines productive farmland, waterfront, and exceptional recreational opportunities. This 105.72-acre agricultural property features approximately 80± acres of tillable ground and is well suited for continued farming, income production, or long-term land investment. The open farmland is framed by wooded perimeter lines with a mixture of mature hardwoods and softwoods, including pine and oak, providing privacy, scenic beauty, and excellent wildlife habitat. The property is zoned agricultural, offering flexibility for farming, recreation, or investment use. Property is being offered in cooperation with Casey Kennedy and Whitetail Properties. The tillable acreage carries an overall NCCPI rating of approximately 57.3, indicating solid, productive ground suitable for row crops, small grains, and conservation programs. The farm boasts over 2,500 feet of water frontage on Miles Creek, offering excellent duck and goose hunting opportunities. The property is located on a known migratory flyway for ducks and geese along the Chesapeake Bay, making it a proven waterfowl destination. A network of trails through the wooded areas leads to a cleared waterfront area on Miles Creek featuring a dock and picnic table, ideal for family activities, swimming, and fishing. A small point along the creek includes a strategically placed booby blind, positioned for effective duck and goose hunting. Additional amenities include multiple duck blinds on Miles Creek and a goose pit. The historic two-story farmhouse, dating to the early 1900s, offers five bedrooms and one full bathroom and features a new roof and siding. Beginning with the main floor, the home offers a large living room, dining room, kitchen, and the first of five bedrooms. The second floor includes four large bedrooms and a full bath. The residence is accessed by a private driveway off Saulsbury Road, providing convenient access while maintaining a high level of privacy. A small shed next to the home provides additional storage. This property is income-producing, with revenue potential from farming operations, CRP enrollment, and hunting leases, making it a versatile investment opportunity, productive farm, or private recreational retreat with waterfront access.

5 Beds ⋅ 1 Baths

Discover one of Talbot County’s rare farms that combines productive farmland, waterfront, and exceptional recreational opportunities. This 105.72-acre agricultural property features approximately 80± acres of tillable ground and is well suited for continued farming, income production, or long-term land investment. The open farmland is framed by wooded perimeter lines with a mixture of mature hardwoods and softwoods, including pine and oak, providing privacy, scenic beauty, and excellent wildlife habitat. The property is zoned agricultural, offering flexibility for farming, recreation, or investment use. Property is being offered in cooperation with Casey Kennedy and Whitetail Properties. The tillable acreage carries an overall NCCPI rating of approximately 57.3, indicating solid, productive ground suitable for row crops, small grains, and conservation programs. The farm boasts over 2,500 feet of water frontage on Miles Creek, offering excellent duck and goose hunting opportunities. The property is located on a known migratory flyway for ducks and geese along the Chesapeake Bay, making it a proven waterfowl destination. A network of trails through the wooded areas leads to a cleared waterfront area on Miles Creek featuring a dock and picnic table, ideal for family activities, swimming, and fishing. A small point along the creek includes a strategically placed booby blind, positioned for effective duck and goose hunting. Additional amenities include multiple duck blinds on Miles Creek and a goose pit. The historic two-story farmhouse, dating to the early 1900s, offers five bedrooms and one full bathroom and features a new roof and siding. Beginning with the main floor, the home offers a large living room, dining room, kitchen, and the first of five bedrooms. The second floor includes four large bedrooms and a full bath. The residence is accessed by a private driveway off Saulsbury Road, providing convenient access while maintaining a high level of privacy. A small shed next to the home provides additional storage. This property is income-producing, with revenue potential from farming operations, CRP enrollment, and hunting leases, making it a versatile investment opportunity, productive farm, or private recreational retreat with waterfront access.

4108 Saulsbury Rd, Trappe

Listing courtesy of VYBE Realty. Contact: 4102204648

$72,500

Tilghman Island. Clear level building lot with public sewer available. The perfect spot for your new vacation / retirement home. Excellent opportunity to make your island dream come true.

21472 Willey Rd, Tilghman

Listing courtesy of Meredith Fine Properties. Contact: 4107149166

$8,750,000

Wilderness Estate- REVISED OFFERING INCLUDES 5 PARCELS 6.27.25- This quintessential Eastern Shore farm is located along the Choptank River in Trappe, Maryland. Comprised of 234 acres, with original structures that are impeccably well-kept and improved with modern amenities, The Wilderness provides a unique opportunity to enjoy the best of the Eastern Shore. Surrounded by open space and preserved farmland with proximity to Oxford, Easton, Cambridge, and St. Michaels, The Wilderness is sure to please the discerning buyer. Sited among large waterfront estates, The Wilderness enjoys privacy and a commanding presence with old-growth trees, broad southerly views, and deep water. The scope of improvements includes the primary residence, waterside guest cottage, beach house, pool, pier, tennis court, early 20th-century barn, and a host of accessory structures for life on the farm. Visit the virtual tour for an inside look and appreciation for the scope of this offering. The main house has great historical significance not only for the original owner’s grandson who lived there and served two terms as the Governor of Maryland but also for its place in the development of Maryland’s domestic architecture, as noted on two markers from the Maryland Bicentennial Commission and the Maryland Historical Society. The smaller and original of the two brick wings dates from the late 18th century and the larger wing from the early 19th century. The house’s architecture is unusual in that the 19th-century wings telescope up, instead of down, from the original wing. The white brick, black shutters, and historical olive green trim color are a serene palette against the house’s majestic specimen trees around the property, including a gigantic Sycamore that is the largest of its species in Maryland. The long white gravel drive under the sheltering canopy of mature trees passes by the barn and other outbuildings then curves around the front of the house. Brick steps lead up to the front porch of the early 19th century wing opening into a gracious foyer and stair hall with an elegant elliptical arch that rests on pilasters at the side walls to separate the public from private areas of the house. A French door at the rear of the foyer frames a vista of the lawn and Choptank River. To the side of the foyer are two identical parlors at the front and rear corners of the house. Both rooms have magnificent fireplace mantles and surround; one is a 1740 hand-carved mantel by noted English artisan woodcarver Grinnling Gibbons and the other is a 1780 mantel surrounded by the famous English architect and artisan, Robert Adam. The main floor of the 18th-century wing contains a spacious living room, dining room, original kitchen, and larger kitchen, pantry, two powder rooms, and a stunning sunroom connecting to a terrace along the rear of the house overlooking the Choptank River. Part of this wing was the final addition to the original home. The second floor of the 19th-century wing contains two bedrooms over the two parlors below with fireplaces and walk-in closets and two baths. The 18th-century wing and later addition contain an artist’s studio with cabinetry and sink that has a myriad uses– TV room, arts and crafts room. The primary suite is located at the rear corner of this wing. It has a fireplace flanked by single windows and another window on the rear wall for panoramic views of the mature landscape and the Choptank River. Two baths complete the suite, with one bath off a hall for access from the art studio. Two stairs access the attic level; one in the 18th-century wing leads to two bedrooms and one bath. The main stair in the 19th-century wing leads to a large game room and another cozy bedroom ensuite. The revised offering of The Wilderness, providing 234 acres comprised of 5 recorded parcels with over 3,000 feet of shoreline is a remarkable opportunity to witness life on the Shore.

6 Beds ⋅ 6 Baths

Wilderness Estate- REVISED OFFERING INCLUDES 5 PARCELS 6.27.25- This quintessential Eastern Shore farm is located along the Choptank River in Trappe, Maryland. Comprised of 234 acres, with original structures that are impeccably well-kept and improved with modern amenities, The Wilderness provides a unique opportunity to enjoy the best of the Eastern Shore. Surrounded by open space and preserved farmland with proximity to Oxford, Easton, Cambridge, and St. Michaels, The Wilderness is sure to please the discerning buyer. Sited among large waterfront estates, The Wilderness enjoys privacy and a commanding presence with old-growth trees, broad southerly views, and deep water. The scope of improvements includes the primary residence, waterside guest cottage, beach house, pool, pier, tennis court, early 20th-century barn, and a host of accessory structures for life on the farm. Visit the virtual tour for an inside look and appreciation for the scope of this offering. The main house has great historical significance not only for the original owner’s grandson who lived there and served two terms as the Governor of Maryland but also for its place in the development of Maryland’s domestic architecture, as noted on two markers from the Maryland Bicentennial Commission and the Maryland Historical Society. The smaller and original of the two brick wings dates from the late 18th century and the larger wing from the early 19th century. The house’s architecture is unusual in that the 19th-century wings telescope up, instead of down, from the original wing. The white brick, black shutters, and historical olive green trim color are a serene palette against the house’s majestic specimen trees around the property, including a gigantic Sycamore that is the largest of its species in Maryland. The long white gravel drive under the sheltering canopy of mature trees passes by the barn and other outbuildings then curves around the front of the house. Brick steps lead up to the front porch of the early 19th century wing opening into a gracious foyer and stair hall with an elegant elliptical arch that rests on pilasters at the side walls to separate the public from private areas of the house. A French door at the rear of the foyer frames a vista of the lawn and Choptank River. To the side of the foyer are two identical parlors at the front and rear corners of the house. Both rooms have magnificent fireplace mantles and surround; one is a 1740 hand-carved mantel by noted English artisan woodcarver Grinnling Gibbons and the other is a 1780 mantel surrounded by the famous English architect and artisan, Robert Adam. The main floor of the 18th-century wing contains a spacious living room, dining room, original kitchen, and larger kitchen, pantry, two powder rooms, and a stunning sunroom connecting to a terrace along the rear of the house overlooking the Choptank River. Part of this wing was the final addition to the original home. The second floor of the 19th-century wing contains two bedrooms over the two parlors below with fireplaces and walk-in closets and two baths. The 18th-century wing and later addition contain an artist’s studio with cabinetry and sink that has a myriad uses– TV room, arts and crafts room. The primary suite is located at the rear corner of this wing. It has a fireplace flanked by single windows and another window on the rear wall for panoramic views of the mature landscape and the Choptank River. Two baths complete the suite, with one bath off a hall for access from the art studio. Two stairs access the attic level; one in the 18th-century wing leads to two bedrooms and one bath. The main stair in the 19th-century wing leads to a large game room and another cozy bedroom ensuite. The revised offering of The Wilderness, providing 234 acres comprised of 5 recorded parcels with over 3,000 feet of shoreline is a remarkable opportunity to witness life on the Shore.

27295 Southside Island Creek Rd, Trappe

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 770-9255